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> First, to pay payroll taxes to employees who live in different states, you have to jump through a bunch of hoops with each state’s government.

While this is a pain and can be costly, isn't it still far cheaper to pay the fees to the states and your accountant than renting an office?

> If I could do it all over again, I probably would have just given each employee an allowance to use on their local state’s open health insurance market

Doing that would save you money by not having to manage the health insurance yourself. It's ridiculous that companies are even responsible for providing health insurance but that's another conversation.

The savings you get from not managing healthcare would probably offset the extra cost of multi-state payroll.



> While this is a pain and can be costly, isn't it still far cheaper to pay the fees to the states and your accountant than renting an office?

Depends on your location. At one point, we had 9 people scattered across multiple states. On one hand, it would have been cheaper to have a small office in an inexpensive location, and force folks to come into an office say, 2 days per week. We’d have been able to ensure that everyone lived in the same place, and avoid the multi-state tax & health care hassles.

We chose to be fully remote because it enabled us to hire better people. The people you want aren’t necessarily in a specific geographic location (nor do they want to move there), and the people you want may have financial incentives to stay where they’re at. The people you want may also choose to live in more expensive areas for quality of life reasons, too.

I found it amusing that, even though we were fully remote and our employees could live in cheap places to maximize their salaries...they didn’t. In fact, we all chose some of the most expensive places in the US to live: downtown Chicago, Manhattan, Miami, San Diego, etc.


This is all true from a straight up numbers perspective, but in my experience, a fixed expense like a 3 year office lease is less stressful than managing fluid expenses like fees imposed by a dozen state governments.

I'm still very pro remote work, but people tend to underestimate how logistically expensive it can be—especially when a team gets bigger—compared to simply leasing an office and saying "Everyone works here."




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